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Cannabidiol synthesis method

A technology of cannabidiol and synthetic methods, which is applied in the direction of organic chemical methods, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of large industrial production limitations and cumbersome steps, and achieve good industrial application prospects and process improvement , cheap effect

Active Publication Date: 2017-06-09
暨明医药科技(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In addition to the above two chemical synthesis methods, there are some reports in the literature that cannabidiol is obtained by biological extraction, but the steps of such methods are relatively cumbersome, and the limitations of industrial production are too large

Method used

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Experimental program
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Effect test

Embodiment 1

[0040] Preparation of intermediate one:

[0041] First, add 119g of 2,4-dihydroxy-6-pentylbenzoic acid methyl ester and 89g of N,N-dimethylethanolamine into a 250mL three-necked flask, add 30.8g of potassium hydroxide under stirring, and nitrogen protection , heated to 130° C. and stirred for 4 hours. Cool the reaction solution below 30°C, adjust the pH to 2-3 with 1N hydrochloric acid aqueous solution, add n-heptane (250mL×2) for extraction, adjust the pH to 10 with solid sodium carbonate in the aqueous phase, add n-heptane (250mL×2) Extract, wash with water (150mL) once, dry over anhydrous sodium sulfate, concentrate to dryness under reduced pressure, add 4v / m n-heptane for recrystallization, obtain 103g after drying, yield 70%, HPLC purity 99.84%.

[0042] Preparation of intermediate two:

[0043] Add 100g of the pure transesterified product and 800mL of dichloromethane into a 2000mL three-necked flask, add 50.8g of zinc chloride and 8g of water under stirring, stir at 25...

Embodiment 2

[0047] Preparation of intermediate one:

[0048] Add 119g of 2,4-dihydroxy-6-pentylbenzoic acid methyl ester and 234g of N,N-dimethylbutanolamine into a 500mL three-necked flask, add 33.6g of potassium hydroxide under stirring, and nitrogen protection , heated to 130° C. and stirred for 4 hours. Cool the reaction solution below 30°C, adjust the pH to 2-3 with 1N hydrochloric acid aqueous solution, add n-heptane (250mL×2) for extraction, adjust the pH to 10 with solid sodium carbonate in the aqueous phase, add n-heptane (250mL×2) Extract, wash with water (150mL) once, dry over anhydrous sodium sulfate, concentrate to dryness under reduced pressure, add 4v / m n-heptane for recrystallization, obtain 134.1g after drying, yield 83%, HPLC purity 99.97%.

[0049] Preparation of intermediate two:

[0050]Put 100g of the pure transesterified product above and 800mL of dichloromethane into a 2000mL three-necked flask, add 46.4g of zinc chloride and 7.3g of water under stirring, stir at...

Embodiment 3

[0054] Preparation of intermediate one:

[0055] Add 119g of 2,4-dihydroxy-6-pentylbenzoic acid methyl ester and 145g of N,N-dimethylhexanolamine into a 250mL three-necked flask, add 30.8g of potassium hydroxide under stirring, and nitrogen protection , heated to 130° C. and stirred for 4 hours. Cool the reaction solution below 30°C, adjust the pH to 2-3 with 1N hydrochloric acid aqueous solution, add n-heptane (250mL×2) for extraction, adjust the pH to 10 with solid sodium carbonate in the aqueous phase, add n-heptane (250mL×2) Extract, wash with water (150mL) once, dry over anhydrous sodium sulfate, concentrate to dryness under reduced pressure, add 4v / m n-heptane for recrystallization, obtain 142.2g after drying, yield 81%, HPLC purity 99.75%.

[0056] Preparation of intermediate two:

[0057] Put 100g of the pure transesterified product above and 800mL of dichloromethane into a 2000mL three-necked flask, add 43.8g of zinc chloride and 6.9g of water under stirring, stir a...

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Abstract

The invention provides a cannabidiol synthesis method. The method includes: taking 2,4-dyhydroxy-6-pentyl methyl benzoate as a raw material, and subjecting to ester exchange with N,N-dialkyl alcohol amine under potassium hydroxide catalysis; subjecting to coupled reaction with (1S, 4R)-1-methyl-4-(1-methylvinyl)-2-cyclohexene-1-alcohol under Lewis acid catalysis; performing acid-base extraction and recrystallization to obtain a high-purity key intermediate product; subjecting to hydrolysis decarboxylation to obtain crude cannabidiol, and subjecting the crude cannabidiol to once recrystallization to obtain cannabidiol according with raw medicine quality requirements. The cannabidiol synthesis method has advantages that raw materials and reagents are cheap and commercially easy to acquire, the total yield of the finally prepared raw medicine in qualified purity reaches 35-40%, the process is improved evidently, and the method has a promising industrial application prospect.

Description

technical field [0001] The invention relates to a synthesis method of cannabidiol, which belongs to the technical field of organic synthesis. Background technique [0002] The alias of cannabidiol is L-trans-cannabidiol, and its English name is (-)-Cannabidiol. It is a very marketable raw material drug. The structural formula of the compound is: [0003] [0004] At present, cannabidiol is mainly used for nerve protection, anti-spasm, anti-inflammatory and anti-anxiety effects. In 2015, the British GW Biopharmaceutical Company announced that it would update its clinical trial data of pure cannabidiol for refractory childhood epilepsy. Severe myoclonic epilepsy, which makes the market prospect of this drug more extensive. It is cheap, efficient and easy to operate, and is suitable for the synthesis process of industrial production, which will also greatly promote the application of cannabidiol. [0005] US20090036523A1 uses olive alcohol as a starting material, catalyze...

Claims

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Application Information

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IPC IPC(8): C07C39/23C07C37/50C07C37/84C07C213/00C07C213/08C07C213/10C07C219/14
CPCC07B2200/07C07C37/50C07C37/84C07C39/23C07C213/00C07C213/08C07C213/10C07C219/14
Inventor 陈剑戈张喜通文小伟徐长春
Owner 暨明医药科技(苏州)有限公司
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